Learning from Friends (and a Few Margaritas Along the Way)

Every few years, I head off on holiday with a group of 10 friends.

Not just any holiday, mind you. We deliberately pick somewhere we wouldn’t normally go, and we drip-feed into a savings pot each month to make it feel that bit more special when it comes around.

This time, it was Mexico’s Caribbean coastline. Tough gig.

What makes these trips particularly interesting is the history. Some of us go back to school days, others to university. There’s a lot of shared experience and, as you’d expect, a lot of catching up to do.

But here’s the thing: even after all that time, I still come back having learned something new about them.

And that got me thinking…

Because, as it happens, more than half of the group now run their own businesses. Which means, somewhere between the beach, the bar, and (inevitably) the third margarita, the conversations start to sound very familiar.

In fact, they mirror almost exactly what we see every month in TAB peer boards.

What stood out?

1. First, there’s a real willingness to be open and honest.
2. Second, there’s a shared understanding that life isn’t plain sailing.
3. Third, different perspectives matter.
4. Fourth, you’ve got to articulate your thinking.
5. Fifth, gratitude gets a look in.

Not always immediately… but give it time (and perhaps a margarita or two), and people start to share what’s really going on.

Even for those whose businesses look incredibly successful from the outside. Especially for those, in fact.

We don’t all agree (thankfully), but that’s where the value lies. Having your thinking challenged—constructively—sharpens decision-making in a way you just can’t replicate on your own.

If you want to bring people with you, you need to explain why you believe what you believe. That discipline alone is hugely valuable.

Even if, like most of us, we’re occasionally guilty of focusing a bit too much on what’s not going right.

And perhaps most importantly... there’s clarity of direction.

The best conversations, and the best decisions, come when you’re clear on where you’re ultimately trying to get to, not just in business, but as an individual.

The common thread? Trust.

None of this works without it. And trust doesn’t appear overnight. It’s built over time. Through shared experiences, consistency, and a willingness to show up as yourself (not just the polished “business owner” version).

Which brings me to something I think is becoming more, not less, important…

Despite the relentless march of AI and technology, the need for us to be properly human with each other hasn’t gone away. If anything, it’s increased.

We still need connection. We still need perspective. We still need people who will challenge us and support us, in equal measure.

So yes, I’d highly recommend a trip to Mexico if you get the chance. But you don’t need a plane ticket to get the benefits.

Invest in your relationships, at home, in your business, and in your wider network. Because when you do, the return isn’t just incremental. It’s exponential. And, unlike a margarita, it keeps paying back long after the glass is empty.